Organophotoredox-catalyzed intermolecular Oxa-[4+2] cycloaddition reactions

Kenta Tanaka; Daichi Omata; Yosuke Asada; Yujiro Hoshino; Kiyoshi Honda

doi:10.1021/acs.joc.9b01156

Organophotoredox-catalyzed intermolecular Oxa-[4+2] cycloaddition reactions

Kenta Tanaka, Daichi Omata, Yosuke Asada, Yujiro Hoshino, Kiyoshi Honda

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

Abstract

An intermolecular oxa-[4+2] cycloaddition reaction promoted by a thioxanthylium photoredox catalyst under irradiation with green light has been developed. The reaction of ortho-quinone methides with styrenes smoothly affords the desired cycloadducts. Especially styrenes bearing electron-donating groups are efficiently transformed in this reaction. This method represents a sustainable way to carry out oxa-[4+2] cycloaddition reactions using only a catalytic amount of a photocatalyst and visible light.

Original language	English
Pages (from-to)	10669-10678
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	84
Issue number	17
DOIs	https://doi.org/10.1021/acs.joc.9b01156
Publication status	Published - Sept 6 2019
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Organophotoredox-catalyzed intermolecular Oxa-[4+2] cycloaddition reactions",

abstract = "An intermolecular oxa-[4+2] cycloaddition reaction promoted by a thioxanthylium photoredox catalyst under irradiation with green light has been developed. The reaction of ortho-quinone methides with styrenes smoothly affords the desired cycloadducts. Especially styrenes bearing electron-donating groups are efficiently transformed in this reaction. This method represents a sustainable way to carry out oxa-[4+2] cycloaddition reactions using only a catalytic amount of a photocatalyst and visible light.",

author = "Kenta Tanaka and Daichi Omata and Yosuke Asada and Yujiro Hoshino and Kiyoshi Honda",

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AU - Tanaka, Kenta

AU - Omata, Daichi

AU - Asada, Yosuke

AU - Hoshino, Yujiro

AU - Honda, Kiyoshi

PY - 2019/9/6

Y1 - 2019/9/6

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AB - An intermolecular oxa-[4+2] cycloaddition reaction promoted by a thioxanthylium photoredox catalyst under irradiation with green light has been developed. The reaction of ortho-quinone methides with styrenes smoothly affords the desired cycloadducts. Especially styrenes bearing electron-donating groups are efficiently transformed in this reaction. This method represents a sustainable way to carry out oxa-[4+2] cycloaddition reactions using only a catalytic amount of a photocatalyst and visible light.

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ER -

Organophotoredox-catalyzed intermolecular Oxa-[4+2] cycloaddition reactions

Abstract

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